CN101514215A - Preparation method and application for ferrocenyl compound sensing material containing amide groups - Google Patents
Preparation method and application for ferrocenyl compound sensing material containing amide groups Download PDFInfo
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- CN101514215A CN101514215A CNA2009100969724A CN200910096972A CN101514215A CN 101514215 A CN101514215 A CN 101514215A CN A2009100969724 A CNA2009100969724 A CN A2009100969724A CN 200910096972 A CN200910096972 A CN 200910096972A CN 101514215 A CN101514215 A CN 101514215A
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- amide
- solution
- sensing material
- ferrocenyl compound
- electrode
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 23
- 239000011540 sensing material Substances 0.000 title claims abstract description 14
- 238000002360 preparation method Methods 0.000 title claims abstract description 8
- 125000003368 amide group Chemical group 0.000 title abstract description 6
- 150000001450 anions Chemical class 0.000 claims abstract description 9
- 230000005518 electrochemistry Effects 0.000 claims abstract description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 24
- 150000001408 amides Chemical class 0.000 claims description 16
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 15
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 10
- KTWOOEGAPBSYNW-UHFFFAOYSA-N ferrocene Chemical compound [Fe+2].C=1C=C[CH-]C=1.C=1C=C[CH-]C=1 KTWOOEGAPBSYNW-UHFFFAOYSA-N 0.000 claims description 9
- 238000004506 ultrasonic cleaning Methods 0.000 claims description 9
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 7
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 239000012044 organic layer Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 229910052786 argon Inorganic materials 0.000 claims description 5
- 229960000935 dehydrated alcohol Drugs 0.000 claims description 5
- 238000001035 drying Methods 0.000 claims description 5
- 239000000706 filtrate Substances 0.000 claims description 5
- 238000000227 grinding Methods 0.000 claims description 5
- 239000010410 layer Substances 0.000 claims description 5
- 238000005498 polishing Methods 0.000 claims description 5
- 238000012360 testing method Methods 0.000 claims description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 2
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical class [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 claims description 2
- 125000000129 anionic group Chemical group 0.000 claims description 2
- 239000008367 deionised water Substances 0.000 claims description 2
- 229910021641 deionized water Inorganic materials 0.000 claims description 2
- 239000000047 product Substances 0.000 claims description 2
- 238000000034 method Methods 0.000 abstract description 2
- FYXKZNLBZKRYSS-UHFFFAOYSA-N benzene-1,2-dicarbonyl chloride Chemical compound ClC(=O)C1=CC=CC=C1C(Cl)=O FYXKZNLBZKRYSS-UHFFFAOYSA-N 0.000 abstract 1
- KVKFRMCSXWQSNT-UHFFFAOYSA-N n,n'-dimethylethane-1,2-diamine Chemical compound CNCCNC KVKFRMCSXWQSNT-UHFFFAOYSA-N 0.000 abstract 1
- 230000035945 sensitivity Effects 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 18
- 150000002500 ions Chemical class 0.000 description 7
- 238000002484 cyclic voltammetry Methods 0.000 description 4
- 238000002242 deionisation method Methods 0.000 description 3
- 239000008151 electrolyte solution Substances 0.000 description 3
- 238000001914 filtration Methods 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 229920006395 saturated elastomer Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 238000001228 spectrum Methods 0.000 description 3
- 238000002848 electrochemical method Methods 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- -1 compound Anion Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
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Abstract
The invention discloses a preparation method and application for ferrocenyl compound sensing material containing amide groups. The ferrocenyl phthaloyl chloride is reacted with the N,N'-dimethylethylenediamine to obtain the ferrocenyl compound containing amide groups, which can be taken as the sensing material identified by the anion in the electrochemistry method and has higher sensitivity for H2PO4<->, HSO4<-> and Br<->.
Description
Technical field
The present invention relates to the sensing material technology of preparing, particularly relate to a kind of ferrocenyl compound sensing material Preparation method and use of amide-containing.
Background technology
Negatively charged ion extensively exists in living things system and living environment, and discerning negatively charged ion effectively is the problem that presses for solution in biomedical and environmental protection field.Electrochemical method because simple to operate, amount of samples is few, low having obtained in Anion Recognition of expense used widely.Electrochemical method requires must to possess the identification receptor that negatively charged ion is discerned the combining unit of an electrochemistry transmission unit and and negatively charged ion effect.Ferrocene group has stable redox characteristic, has been proved to be one of the most effective electrochemical signals transport group.In addition, amide group has a hydrogen-bond donor, can combine with negatively charged ion very effectively, is a kind of common negatively charged ion combining unit.Therefore, design contains emphasis and the focus that the anion receptor of the ferrocene-containing compound of amide group is research always.
Summary of the invention
The object of the present invention is to provide a kind of ferrocenyl compound sensing material Preparation method and use of amide-containing, by ferrocene dimethyl chloride and N, a kind of ferrocenyl compound of amide-containing is synthesized in N '-dimethyl-ethylenediamine reaction, obtains a kind of ferrocenyl compound Anion Recognition sensing material of amide-containing.
The technical solution used in the present invention is as follows:
One, a kind of ferrocenyl compound sensing material preparation method of amide-containing, the step of this method is as follows:
(1) synthetic ferrocene dimethyl chloride; (Zhi Yonggang, Dong Chune etc. chemical research and application [J] .2000,12,413-416)
(2) room temperature, under the argon shield, adding concentration in container is the N of 1.4mol/L, the dichloromethane solution of N '-dimethyl-ethylenediamine;
(3) with triethylamine, concentration is that the dichloromethane solution of the ferrocene dimethyl chloride of 0.14mol/L joins in the solution of step (1) successively, and three's volume ratio is 23: 1: 50;
(4) room temperature reaction is 12 hours, stopped reaction;
(5) filter, filtrate is used saturated sodium bicarbonate solution and deionized water wash twice respectively, takes off a layer organic layer;
(6) after organic layer dewatered with anhydrous magnesium sulfate drying, the rotation evaporate to dryness obtained the brown product;
Two, a kind of purposes of ferrocenyl compound sensing material of amide-containing: the sensing material as the electrochemistry Anion Recognition carries out Anion Recognition, and its step is as follows:
(1) configuration [Fe] concentration is the dichloromethane solution of the ferrocenyl compound of 0.5mmol/L amide-containing;
(2) working electrode Al
2O
3Grinding and polishing is used NaOH, HNO then successively
3, dehydrated alcohol, secondary redistilled water ultrasonic cleaning dry, and reference electrode and supporting electrode ultrasonic cleaning dried;
(3) fill electrolyzer with the dichloromethane solution of the ferrocenyl compound of amide-containing in the step (1), form three-electrode system, will contain the anionic CH of 0.25mol/L by working electrode, reference electrode and supporting electrode
2Cl
2Solution joins in the electrolyzer, carries out the test of electrochemistry Anion Recognition on the comprehensive electrochemical analyser of CHI-630A.
The beneficial effect that the present invention has is:
(1) this is a kind of ferrocenyl compound that contains amide group;
(2) negatively charged ion of being discerned is H
2PO
4 -, HSO
4 -And Br
-
(3) main Anion Recognition testing method is an electrochemical cyclic voltammetry.
Description of drawings
Fig. 1 is the ferrocenyl compound 1-Fc of amide-containing
1The H nuclear magnetic resonance map.
Fig. 2 is that the ferrocenyl compound 1-Fc of amide-containing is along with H
2PO
4 -The electrochemical behavior that adds. (1) H
2PO
4 -/ 1-Fc=0; (2) H
2PO
4 -/ 1-Fc=0.4; (3) H
2PO
4 -/ 1-Fc=0.8; (4) H
2PO
4 -/ 1-Fc=1.0; (5) H
2PO
4 -/ 1-Fc=1.4;
Fig. 3 is that the ferrocenyl compound 1-Fc of amide-containing is along with HSO
4 -The electrochemical behavior that adds. (1) HSO
4 -/ 1-Fc=0; (2) HSO
4 -/ 1-Fc=0.8; (3) HSO
4 -/ 1-Fc=1.4; (4) HSO
4 -/ 1-Fc=2.4; (5) HSO
4 -/ 1-Fc=3.4; (6) HSO
4 -/ 1-Fc=5.0.
Embodiment
Enumerate several specific embodiments below and further set forth the present invention.
Embodiment 1:
Argon shield under the room temperature, adds the N of 3ml (0.028mol), the CH that N '-dimethyl-ethylenediamine, 20ml handled successively in the two neck bottles of 100ml
2Cl
2And the triethylamine of 1ml (0.007mol), Dropwise 5 0ml contains the CH of the ferrocene dimethyl chloride of 1.785g (0.007mol) lentamente then
2Cl
2Solution, stopped reaction behind the room temperature reaction 12h.After the filtration, filtrate is used saturated NaHCO respectively
3Solution and deionization washed twice are taken off a layer organic layer, use anhydrous MgSO
4After drying dewatered, the rotation evaporate to dryness obtained the brown solid.
1The HNMR spectrum as shown in Figure 1.
With working electrode with 0.05 μ m Al
2O
3Al
2O
3Grinding and polishing is used NaOH, HNO more successively to minute surface
3, dehydrated alcohol, secondary redistilled water ultrasonic cleaning dry, and reference electrode and supporting electrode ultrasonic cleaning dried.Prepare 0.25mol/L Bu earlier
4NH
2PO
4CH
2Cl
2Solution, a certain amount of with the each dropping of microsyringe then is [Fe]=0.5mmol/L to ferrocenyl compound concentration, with 0.1mol/L[n-Bu
4N] BF
4Be electrolytical CH
2Cl
2In the electrolytic solution.On the comprehensive electrochemical analyser of CHI-630A, carry out electrochemical cyclic voltammetry and measure scanning.The CV curve as shown in Figure 2.
Embodiment 2:
Argon shield under the room temperature, adds the N of 6ml (0.056mol), the CH that N '-dimethyl-ethylenediamine, 40ml handled successively in the two neck bottles of 200ml
2Cl
2And the triethylamine of 2ml (0.014mol), drip the CH that 100ml contains the ferrocene dimethyl chloride of 3.57g (0.014mol) then lentamente
2Cl
2Solution, stopped reaction behind the room temperature reaction 12h.After the filtration, filtrate is used saturated NaHCO respectively
3Solution and deionization washed twice are taken off a layer organic layer, use anhydrous MgSO
4After drying dewatered, the rotation evaporate to dryness obtained the brown solid.
1The HNMR spectrum as shown in Figure 1.
With working electrode with 0.05 μ m Al
2O
3Al
2O
3Grinding and polishing is used NaOH, HNO more successively to minute surface
3, dehydrated alcohol, secondary redistilled water ultrasonic cleaning dry, and reference electrode and supporting electrode ultrasonic cleaning dried.Prepare 0.25mol/L Bu earlier
4NHSO
4CH
2Cl
2Solution, a certain amount of with the each dropping of microsyringe then is [Fe]=0.5mmol/L to ferrocenyl compound concentration, with 0.1mol/L[n-Bu
4N] BF
4Be electrolytical CH
2Cl
2In the electrolytic solution.On the comprehensive electrochemical analyser of CHI-630A, carry out electrochemical cyclic voltammetry and measure scanning.The CV curve as shown in Figure 3.
Embodiment 3:
Argon shield under the room temperature, adds the N of 15ml (0.14mol), the CH that N '-dimethyl-ethylenediamine, 100ml handled successively in the two neck bottles of 500ml
2Cl
2And the triethylamine of 5ml (0.035mol), drip the CH that 250ml contains the ferrocene dimethyl chloride of 8.925g (0.035mol) then lentamente
2Cl
2Solution, stopped reaction behind the room temperature reaction 12h.After the filtration, filtrate is used saturated NaHCO respectively
3Solution and deionization washed twice are taken off a layer organic layer, use anhydrous MgSO
4After drying dewatered, the rotation evaporate to dryness obtained the brown solid.
1The HNMR spectrum as shown in Figure 1.
With working electrode with 0.05 μ m Al
2O
3Al
2O
3Grinding and polishing is used NaOH, HNO more successively to minute surface
3, dehydrated alcohol, secondary redistilled water ultrasonic cleaning dry, and reference electrode and supporting electrode ultrasonic cleaning dried.Prepare 0.25mol/L Bu earlier
4The CH of NBr
2Cl
2Solution, a certain amount of with the each dropping of microsyringe then is [Fe]=0.5mmol/L to ferrocenyl compound concentration, with 0.1mol/L[n-Bu
4N] BF
4Be electrolytical CH
2Cl
2In the electrolytic solution.On the comprehensive electrochemical analyser of CHI-630A, carry out electrochemical cyclic voltammetry and measure scanning.
Claims (2)
1. the ferrocenyl compound sensing material preparation method of an amide-containing is characterized in that, the step of this preparation is as follows:
(1) room temperature, under the argon shield, adding concentration in container is the N of 1.4mol/L, the dichloromethane solution of N '-dimethyl-ethylenediamine;
(2) with triethylamine, concentration is that the dichloromethane solution of the ferrocene dimethyl chloride of 0.14mol/L joins in the solution of step (1) successively, and three's volume ratio is 23: 1: 50;
(3) room temperature reaction is 12 hours, stopped reaction;
(4) filter, filtrate is used saturated sodium bicarbonate solution and deionized water wash twice respectively, takes off a layer organic layer;
(5) after organic layer dewatered with anhydrous magnesium sulfate drying, the rotation evaporate to dryness obtained the brown product.
2. the purposes of the ferrocenyl compound sensing material of an amide-containing, it is characterized in that: the sensing material as the electrochemistry Anion Recognition carries out Anion Recognition, and its step is as follows:
(1) configuration [Fe] concentration is the dichloromethane solution of the ferrocenyl compound of 0.5mmol/L amide-containing;
(2) working electrode Al
2O
3Grinding and polishing is used NaOH, HNO then successively
3, dehydrated alcohol, secondary redistilled water clean under ultrasonic wave and dry, and reference electrode and supporting electrode are dried under ultrasonic cleaning;
(3) fill electrolyzer with the dichloromethane solution of the ferrocenyl compound of amide-containing in the step (1), form three-electrode system, will contain the anionic CH of 0.25mol/L by working electrode, reference electrode and supporting electrode
2Cl
2Solution joins in the electrolyzer, carries out the test of electrochemistry Anion Recognition on the comprehensive electrochemical analyser of CHI-630A.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNA2009100969724A CN101514215A (en) | 2009-03-26 | 2009-03-26 | Preparation method and application for ferrocenyl compound sensing material containing amide groups |
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|---|---|---|---|
| CNA2009100969724A CN101514215A (en) | 2009-03-26 | 2009-03-26 | Preparation method and application for ferrocenyl compound sensing material containing amide groups |
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044493A (en) * | 2012-12-18 | 2013-04-17 | 中国科学院上海有机化学研究所 | Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof |
| CN103483392A (en) * | 2013-08-25 | 2014-01-01 | 浙江大学 | Polymer microsphere with hollow structure as well as preparation method and hydrogen storage use thereof |
| CN105301084A (en) * | 2015-10-09 | 2016-02-03 | 桂林理工大学 | Ferrocene side chain-containing benzophenanthrene anion identifying agent and application thereof |
-
2009
- 2009-03-26 CN CNA2009100969724A patent/CN101514215A/en active Pending
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN103044493A (en) * | 2012-12-18 | 2013-04-17 | 中国科学院上海有机化学研究所 | Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof |
| CN103044493B (en) * | 2012-12-18 | 2015-04-29 | 中国科学院上海有机化学研究所 | Acrylamide type monomer containing dicyclopentadienyl iron structure, as well as amphipathic polymer, preparation method and use thereof |
| CN103483392A (en) * | 2013-08-25 | 2014-01-01 | 浙江大学 | Polymer microsphere with hollow structure as well as preparation method and hydrogen storage use thereof |
| CN105301084A (en) * | 2015-10-09 | 2016-02-03 | 桂林理工大学 | Ferrocene side chain-containing benzophenanthrene anion identifying agent and application thereof |
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Open date: 20090826 |